N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide → N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 1184877Notes

Reaction equation

HRID 1184877 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[N+:21]([O-])=O>[Pd].CO.[H][H]>[NH2:21][C:3]1[CH:4]=[C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=2)[CH:6]=[CH:7][C:2]=1[CH3:1]

Participants

5

Reactant 1

HCID 11716802N-(4-Methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide

Product 1

HCID 11529455N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamideYield 110.2%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 178418361HCID 178418361, compoundSolvent

Procedure

To a mixture of N-(4-methyl-3-nitrophenyl)-3-(trifluoromethyl)benzamide 66 (12 g, 37.0 mmol) and palladium on activated carbon (0.438 g, 3.70 mmol) in methanol (800 mL), hydrogen (gas) was bubbled through for 2 h. Excess of Pd/C (5 g) was added and stirred for additional 2 h. Filtered over decalite and concentrated to give N-(3-amino-4-methylphenyl)-3-(trifluoromethyl)benzamide 67 (12 g, 88%). (m/z)=295 (M+H)+.

Workup

  1. customwas bubbled through for 2 h
  2. additionExcess of Pd/C (5 g) was added
  3. filtrationFiltered over decalite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-92b091cc360744348dd898c508119822
Source dataset
uspto-grants-2014_03
Patent number
US08669256B2

Reaction notes

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